Photochemical reactions of benzothiazole-2-thiones
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 2197-2200
- https://doi.org/10.1039/p19930002197
Abstract
The photochemical reactions of benzothiazole-2-thiones in the presence of alkenes have been examined. Irradiation of N-unsubstituted benzothiazole-2-thione in the presence of electron-poor alkenes gave 2-substituted benzothiazoles. Irradiation of N-substituted benzothiazole-2-thiones and electron-poor alkenes yielded 2-alkylidenebenzothiazoles and the unexpected spiro-1,3-dithianes. The formation of these photoproducts can be explained in terms of the intermediacy of aminospirothietanes, which are derived by [2 + 2] photocycloaddition of the CS bond of benzothiazole-2-thiones to the CC bond of alkenes.Keywords
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